US20050059759A1 - Method of gluing hydrophobic and oleophobic substrates which are intended for packaging - Google Patents
Method of gluing hydrophobic and oleophobic substrates which are intended for packaging Download PDFInfo
- Publication number
- US20050059759A1 US20050059759A1 US10/815,914 US81591404A US2005059759A1 US 20050059759 A1 US20050059759 A1 US 20050059759A1 US 81591404 A US81591404 A US 81591404A US 2005059759 A1 US2005059759 A1 US 2005059759A1
- Authority
- US
- United States
- Prior art keywords
- styrene
- adhesive
- phase
- compatible
- encompassed
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000758 substrate Substances 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000004026 adhesive bonding Methods 0.000 title claims abstract description 16
- 238000004806 packaging method and process Methods 0.000 title claims abstract description 15
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000000853 adhesive Substances 0.000 claims abstract description 64
- 230000001070 adhesive effect Effects 0.000 claims abstract description 64
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000004014 plasticizer Substances 0.000 claims abstract description 9
- 229920006132 styrene block copolymer Polymers 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims description 27
- 239000011111 cardboard Substances 0.000 claims description 21
- -1 ethylene, propylene, isoprene Chemical class 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000001993 wax Substances 0.000 claims description 12
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 9
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 9
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920001400 block copolymer Polymers 0.000 claims description 9
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 9
- 239000004698 Polyethylene Substances 0.000 claims description 8
- 229920000573 polyethylene Polymers 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 5
- 239000004743 Polypropylene Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000004200 microcrystalline wax Substances 0.000 claims description 4
- 235000019808 microcrystalline wax Nutrition 0.000 claims description 4
- 229920001083 polybutene Polymers 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 125000005498 phthalate group Chemical class 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 150000003097 polyterpenes Chemical class 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 239000000654 additive Substances 0.000 abstract description 4
- 229920002633 Kraton (polymer) Polymers 0.000 description 9
- 239000011324 bead Substances 0.000 description 9
- 239000004831 Hot glue Substances 0.000 description 8
- 239000003292 glue Substances 0.000 description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 8
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 8
- 239000005038 ethylene vinyl acetate Substances 0.000 description 7
- XPVIQPQOGTVMSU-UHFFFAOYSA-N (4-acetamidophenyl)arsenic Chemical compound CC(=O)NC1=CC=C([As])C=C1 XPVIQPQOGTVMSU-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920013640 amorphous poly alpha olefin Polymers 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- 239000011087 paperboard Substances 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000002655 kraft paper Substances 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000011436 cob Substances 0.000 description 2
- 230000008094 contradictory effect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000013011 mating Effects 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/02—Vinyl aromatic monomers and conjugated dienes
- C09J153/025—Vinyl aromatic monomers and conjugated dienes modified
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
Definitions
- This invention has as its object a process for gluing together substrates that are made oleophobic and hydrophobic, using an adhesive based on styrene block copolymers. It also has as its object adhesives that make possible the gluing of so-called difficult substrates such as those made oleophobic and hydrophobic.
- HMA Hot Melt Adhesives
- the polymer that is used in the HMA consists of, for example, the ethylene-type copolymers, such as vinyl ethylene-acetate (EVA), amorphous poly-alpha-olefins (APAO), polyolefins that are synthesized by metallocene catalysis, polyethylenes of low molecular weight or else amorphous polypropylenes.
- EVA vinyl ethylene-acetate
- APAO amorphous poly-alpha-olefins
- polyolefins that are synthesized by metallocene catalysis
- polyethylenes of low molecular weight or else amorphous polypropylenes ethylenes of low molecular weight or else amorphous polypropylenes.
- styrene block copolymers where the latter is combined with a co-monomer such as isoprene or butadiene, hydrogenated forms of these components.
- the selection will naturally be made on a criterion of structural
- the preparation of food products for example, as well as their preservation or the conditions in which they are stored, require that the packaging be resistant and continue to ensure its function under extreme temperatures.
- the gluing should be effective during all of the packaging operations or the life cycle of the packaging.
- fluorinated compounds such as the fluorinated polyacrylates in the treatment of substrates that are intended for packaging so as to impart to them oleophobic and hydrophobic barrier properties, namely both at a high level of resistance to water and a high level of resistance to oils and fatty substances.
- fluorinated compounds of various types are used in an aqueous phase and are therefore hydrodilutable. They are either small fluorinated molecules, for example fluorinated phosphate salts, or fluorinated sulfate salts, or fluorinated acrylic copolymers, i.e., copolymers of which at least one monomer comprises a perfluorinated group, whereby the other non-fluorinated monomers are acrylic or vinyl.
- fluorinated lattices i.e., dispersions of copolymers in water in the presence of surfactant, either hydrosoluble or hydrodispersible copolymers, in general copolymers of cationic type.
- fluorinated compounds are used either in the body of the substrate, for example, paper, or as a coating for said substrate.
- the adhesive should be able to meet a whole series of sometimes contradictory stresses that are linked to both conditions of use of the packaging and to the nature of the various substrates that are used, identical or different or composite materials, most of the time based on paper or cardboard, but also metal (aluminum) or plastics (polyethylene, polypropylene, terephthalate polyethylene, polystyrene . . . ) of which at least one is a substrate that is made difficult by a treatment based on fluorinated compounds such as fluorinated polyacrylates. It is also necessary to add that the operating conditions for glue application play an important role.
- the adhesive should be able to be used for any assembly of which at least one of the substrates has undergone a hydrophobic and oleophobic treatment.
- the adhesive should therefore have very specific and sometimes contradictory characteristics, short setting time, good wetting power, very good thermal behavior of the adhesion after temperature cycles located between ⁇ 10° C. and +60° C., and even between ⁇ 40° C. and +80° C., as well as a low viscosity because of the fluorinated treatment.
- the process according to the invention is used in the sense of resolving this problem, in particular by a selection of the polymer and its structure.
- the invention has as its object a process for gluing together so-called difficult substrates that are intended for the manufacture of packages, which consists in applying on at least one of the substrates an adhesive that comprises:
- the adhesive of the process of the invention optionally can comprise various additives such as antioxidants. . . .
- Component a) according to the process of the invention has a diblock, triblock or multiblock, linear, radial or star-shaped structure, whereby the intermediate block consists of at least one of the comonomers listed above and can undergo a hydrogenation phase.
- Component a) is preferably a styrene-ethylene butylene-styrene block copolymer (designated SEBS) or any other close structure. It is possible to mix this
- component a) with other polymers such as the copolymers of ethylene, polyolefins, polymers that are obtained by a metallocene catalysis path.
- the content of the adhesive in component a) in general between 5 and 50% by mass is preferably between 15 and 30%.
- component b) is selected from among the resins that are conventionally used in the thermofusible adhesives, such as:
- Component c) consists of resin or a mixture of resins that are conventionally used, such as the polymers that are obtained from aromatic fractions or else poly-alpha-methylstyrene. It is preferably selected from among the resins that are obtained from the polymerization of alpha-methylstyrene, for example having a softening point that is measured according to the EN 1238 standard encompassed between 80 and 160° C.
- the content of component c) is between 0 and 20% by mass and preferably between 5 and 15%.
- Component d) is selected for the most part from among the so-called microcrystalline waxes that are conventionally used in the thermofusible adhesives, having a melting point (ASTM D127 method) of between 70 and 100° C., preferably between 80 and 95° C.
- component d) can contain synthesis waxes such as polyolefins with short chains that are rather linear, obtained by polymerization according to standard processes (Ziegler Natta; Fischer Tropsch), whose melting point that is measured according to the standard (ASTM D127 method) is high, generally between 80 and 150° C. and preferably between 90 and 120° C.
- the content of component d) is between 5 and 25%, and preferably between 10 and 17% by mass.
- Polymers of another nature can be present in a minority way in the adhesive, for example the ethylene-vinyl acetate copolymers (EVA), the polyolefins of the processes or of various natures, and the other styrene block copolymers.
- EVA ethylene-vinyl acetate copolymers
- polyolefins of the processes or of various natures for example the ethylene-vinyl acetate copolymers (EVA), the polyolefins of the processes or of various natures, and the other styrene block copolymers.
- the various additives will be, for example, the antioxidants that are conventionally used in the thermofusible adhesives or in the industry for transformation of thermoplastic compounds, such as hindered phenolic derivatives, phosphites or mixtures thereof.
- the viscosity of the thermofusible adhesive of the process of the invention will be between 400 and 3000 mPa.s at 170° C. and preferably between 700 and 1400. Its softening point that is measured according to the so-called ball-ring method that is known to one skilled in the art will be encompassed between 75 and 120° C.
- the adhesive according to the process of the invention is obtained by mixing a), b), c), d) and e) as well as the possible additives, by any suitable means, for example by a simple mixing at a temperature of between 150 and 170° C.
- the adhesive can be easily characterized by chemical analysis according to the standard processes for deformulation and identification of different fractions, in particular by infra-red spectrometry, nuclear magnetic resonance 1H and 13C, elementary micro-analysis, gel permeation chromatography or high-performance chromatography or else by differential calorimetry (DSC or Differential Scanning Calorimetry).
- the adhesives of the process of the invention are applied according to the standard methods that are used in the area of thermofusible adhesives, on the packaging chain or else on the edge of the latter.
- Starting from a boiler tank via heated and heat-insulated pipes, by extrusion nozzles: controlled deposition of one or more beads on a first substrate and mating with the second substrate, with optional pressing of the adhesive joint thus produced.
- the low-viscosity HMA can be applied by any other possible means such as, for example, a lipped nozzle, multi-line nozzles, disk, imprint or else by the Sift Proof process developed by the Nordson Company.
- the temperature of the adhesive at the time of application is conventionally between 150 and 180° C.
- the machine open time is the time that passes between the application of the adhesive on the first substrate and mating with the second substrate.
- the machine pressing time is the time immediately after gluing during which the two glued substrates are kept in contact with a force that is at least equal to the force of reopening the packaging without adhesive.
- the adhesive is applied on thin substrates, i.e., of a thickness that is generally encompassed between 0.05 and about 2 mm, whereby these substrates can be part of a thicker complex structure.
- This substrate often can be based on paper or cardboard, such as virgin or recycled kraft paper, having a low density or on the contrary a compact thin substrate, optionally treated by fluorinated compounds or on the surface by acrylic varnish or UV-reticulated varnish, or of specific coatings, optionally with non-coated zones, reserves, to make possible the deposition and the hooking of the adhesive on the substrate.
- the nature of the various substrates used is selected from among identical or different or composite materials, most of the time based on paper or cardboard, metal, for example, aluminum, or plastics, such as polyethylene, polypropylene, terephthalate polyethylene, polystyrene,. . . .
- the substrates that are used for our tests are FORAPERLED® 325 treated papers or cardboards with a concentration of about 3%.
- the raw materials that are used in the examples are as follows: Kraton ® G1652 Copolymer of ethylene-butylene and styrene, Melt Index 10, % styrene 30 and no diblock, marketed by Kraton Polymers Kraton ® G1726 Copolymer of ethylene-butylene and styrene, Melt Index 65, % styrene 30 and 70% diblock, marketed by Kraton Polymers Kraton ® G1657 Copolymer of ethylene-butylene and styrene, Melt Index 8, % styrene 13 and 30% diblock, marketed by Kraton Polymers Evatane ® 18-500 EVA Melt Index 500, vinyl acetate 18%, marketed by Atofina Evatane ® 28-420 EVA Melt Index 420, vinyl acetate 28%, marketed by Atofina Evatane ® 33-400 EVA Melt Index 400, vinyl acetate
- testM E 28 marketed by Hercules Norsolène ® Resin that is obtained from the polymerization of pure monomers W110 of ⁇ methyl-styrene, softening point 105-115° C. (ISO 4625), marketed by Cray Valley Foral ® AX-E Resin that is obtained from the hydrogenated rosin, softening point 81° C. (ASTM E 28), marketed by Hercules Foral ® 85-E Resin that is obtained from the hydrogenated and glycerol- esterified rosin, softening point 85° C.
- ASTM E 28 marketed by Hercules Dertophène ® T Phenolic terpene resin that is obtained from the condensation of terebenthine gasolines with phenol, softening point 95° C.
- ASTM E28 marketed by DRT Dertoline ® DEG 2 Resin that is obtained from the hydrogenated and diethylene glycol-esterified rosin, softening point 35° C.
- DRT Sylvarley ® 540 Resin that is obtained by copolymerization of styrene with ⁇ methyl-styrene or vinyl-toluene, softening point 75° C., marketed by Arizona Chemical Besquare ® 185 So-called microcrystalline wax, consisting of saturated hydrocarbons with branched and cyclized chains, softening point about 90° C.
- Examples 1 and 2 target first-generation adhesives of the prior art based on EVA (Example 1) and APAO (Example 2);
- Examples 3 and 4 are comparison examples that use SEBS bases described in the prior art and Examples 5 and 6 of the examples based on SEBS according to the process of the invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Wrappers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/124,036 US20080221247A1 (en) | 2001-10-02 | 2008-05-20 | Method of gluing hydrophobic and oleophobic substrates which are intended for packaging |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0112654A FR2830257B1 (fr) | 2001-10-02 | 2001-10-02 | Procede d'assemblage par collage de substrats hydrophobes et oleophobes destines au marche de l'emballage |
| FR01/12654 | 2001-10-02 | ||
| PCT/FR2002/003335 WO2003029379A1 (fr) | 2001-10-02 | 2002-10-01 | Procede d'assemblage par collage de substrats hydrophobes et oleophobes destines au marche de l'emballage |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR2002/003335 Continuation WO2003029379A1 (fr) | 2001-10-02 | 2002-10-01 | Procede d'assemblage par collage de substrats hydrophobes et oleophobes destines au marche de l'emballage |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/124,036 Continuation US20080221247A1 (en) | 2001-10-02 | 2008-05-20 | Method of gluing hydrophobic and oleophobic substrates which are intended for packaging |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20050059759A1 true US20050059759A1 (en) | 2005-03-17 |
Family
ID=8867836
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/815,914 Abandoned US20050059759A1 (en) | 2001-10-02 | 2004-04-02 | Method of gluing hydrophobic and oleophobic substrates which are intended for packaging |
| US12/124,036 Abandoned US20080221247A1 (en) | 2001-10-02 | 2008-05-20 | Method of gluing hydrophobic and oleophobic substrates which are intended for packaging |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/124,036 Abandoned US20080221247A1 (en) | 2001-10-02 | 2008-05-20 | Method of gluing hydrophobic and oleophobic substrates which are intended for packaging |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20050059759A1 (fr) |
| EP (1) | EP1434829A1 (fr) |
| JP (1) | JP2005504164A (fr) |
| AU (1) | AU2002350812B2 (fr) |
| FR (1) | FR2830257B1 (fr) |
| WO (1) | WO2003029379A1 (fr) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060229411A1 (en) * | 2005-04-06 | 2006-10-12 | Stephen Hatfield | Hot melt pressure sensitive adhesives based on blends of styrene/butadiene copolymers |
| WO2008028716A1 (fr) * | 2006-09-05 | 2008-03-13 | Henkel Ag & Co. Kgaa | Étiquettes redécollables |
| US20110020634A1 (en) * | 2008-04-28 | 2011-01-27 | Sika Technology Ag | Hotmelt adhesives having an extended open time |
| US20140199908A1 (en) * | 2011-09-16 | 2014-07-17 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
| US20140329074A1 (en) * | 2011-12-19 | 2014-11-06 | Sika Technology Ag | Reactive polyolefin hot-melt adhesive having low viscosity and use thereof for textile laminations |
| US9695340B2 (en) | 2011-09-16 | 2017-07-04 | Henkel Ag & Co. Kgaa | Low temperature hot melt adhesive for high-speed coating and spiral coating |
| US9758704B2 (en) | 2012-08-28 | 2017-09-12 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
| US9816014B2 (en) | 2011-09-16 | 2017-11-14 | Henkel Ag & Co. Kgaa | Hot melt adhesive for disposable products |
| CN115806789A (zh) * | 2022-09-26 | 2023-03-17 | 嘉好(太仓)新材料股份有限公司 | 一种用于口罩耳带粘接热熔胶及其制备方法 |
| DE102023126363A1 (de) | 2023-09-27 | 2025-03-27 | Tesa Se | Haftklebemasse und wiederablösbare Selbstklebeprodukte umfassend die Haftklebemasse |
| EP4621025A1 (fr) * | 2024-03-21 | 2025-09-24 | Colquimica-Indústria Nacional de Colas, S.A. | Adhésif thermofusible en granulés ou en perles pour coller les bouchons aux capsules et son procédé de fabrication |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622523B2 (en) | 2002-08-12 | 2009-11-24 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
| JP2005535748A (ja) | 2002-08-12 | 2005-11-24 | エクソンモービル・ケミカル・パテンツ・インク | 可塑性ポリオレフィン組成物 |
| US7531594B2 (en) | 2002-08-12 | 2009-05-12 | Exxonmobil Chemical Patents Inc. | Articles from plasticized polyolefin compositions |
| US7271209B2 (en) | 2002-08-12 | 2007-09-18 | Exxonmobil Chemical Patents Inc. | Fibers and nonwovens from plasticized polyolefin compositions |
| FR2867160B1 (fr) * | 2004-03-05 | 2006-07-14 | Oreal | Emballage revetu d'un vernis de protection vis-a-vis de la lumiere |
| FR2882681B1 (fr) * | 2005-03-03 | 2009-11-20 | Coriolis Composites | Tete d'application de fibres et machine correspondante |
| US8163192B2 (en) * | 2009-06-26 | 2012-04-24 | Vincelli Sr Fred | Hydroseed substrate and method of making such |
| US8163194B2 (en) | 2009-06-26 | 2012-04-24 | Vincelli Sr Fred | Hydroseed substrate and method of making such |
| CN104715830A (zh) * | 2015-03-11 | 2015-06-17 | 上海军信船舶科技有限公司 | 一种电缆用水密封热熔胶及其应用 |
| CN112513215B (zh) * | 2018-07-24 | 2023-04-18 | 汉高股份有限及两合公司 | 具有较低熔体粘度的热熔粘合剂组合物 |
| JP7694147B2 (ja) * | 2021-05-24 | 2025-06-18 | artience株式会社 | 樹脂組成物及び該樹脂組成物を用いた積層体 |
Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917607A (en) * | 1971-09-22 | 1975-11-04 | Shell Oil Co | Block copolymer adhesive compositions |
| US4394915A (en) * | 1982-04-12 | 1983-07-26 | Findley Adhesives Inc. | Hot melt adhesive compositions and bottle assemblies using said compositions |
| US5095059A (en) * | 1990-03-28 | 1992-03-10 | Mitsui Toatsu Chemicals, Inc. | Oiled-face adherable, hot-melt adhesive composition and a non-slip processing method of metal scaffolding board |
| US5120585A (en) * | 1990-10-12 | 1992-06-09 | Gelman Sciences Technology, Inc. | Package for preservative agent |
| US5120781A (en) * | 1991-05-07 | 1992-06-09 | Union Camp Corporation | Acid-modified polyhydric alcohol rosin ester tackifiers and hot melt adhesive compositions containing those tackifiers |
| US5266400A (en) * | 1990-04-20 | 1993-11-30 | Minnesota Mining And Manufacturing Company | Low voltage electron beam radiation cured elastomer-based pressure sensitive adhesive tape |
| US5496628A (en) * | 1992-11-25 | 1996-03-05 | Textiles Coated Incorporated | Single membrane insulation material |
| US5863977A (en) * | 1993-10-12 | 1999-01-26 | H. B. Fuller Licensing & Financing, Inc. | High molecular weight S-EB-S hot melt adhesive |
| US5910527A (en) * | 1994-04-28 | 1999-06-08 | Ato Findley, Inc. | Hot melt adhesive having a high acid number for disposable soft goods |
| US5939483A (en) * | 1996-07-12 | 1999-08-17 | H.B. Fuller Licensing & Financing, Inc. | Low application temperature hot melt with excellent heat and cold resistance |
| US6121354A (en) * | 1998-11-19 | 2000-09-19 | Bostik, Inc. | High performance single-component sealant |
| US6232391B1 (en) * | 1998-12-23 | 2001-05-15 | National Starch And Chemical Investment Holding Corporation | Multipurpose hot melt adhesive |
| US6291571B1 (en) * | 2000-03-21 | 2001-09-18 | Adco Products, Inc. | Lap edge roofing sealant |
| US6448303B1 (en) * | 2000-12-29 | 2002-09-10 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives for dermal application |
| US6582829B1 (en) * | 1996-03-14 | 2003-06-24 | H.B. Fuller Licensing & Financing Inc. | Hot melt adhesive composition comprising homogeneous ethylene interpolymer and block copolymer |
| US6926959B2 (en) * | 2000-01-31 | 2005-08-09 | H. B. Fuller Licensing & Financing, Inc. | Radiation curable adhesive compositions comprising block copolymers having vinyl functionalized polydiene blocks |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5149741A (en) * | 1989-07-21 | 1992-09-22 | Findley Adhesives, Inc. | Hot melt construction adhesives for disposable soft goods |
| KR930017965A (ko) * | 1992-02-28 | 1993-09-21 | 핀들리 어드히시브, 인코포레이티드 | 냉유동 접착제 조성물을 포장하기 위한 필름 |
| EP0781824B1 (fr) * | 1995-12-27 | 2001-07-25 | Central Glass Company, Limited | Adhésif pour lier une résine de fluorure de vinylidène à un substrat |
| JP4034478B2 (ja) * | 1999-07-02 | 2008-01-16 | スリーエム イノベイティブ プロパティズ カンパニー | 感圧接着シート及びその製造方法 |
-
2001
- 2001-10-02 FR FR0112654A patent/FR2830257B1/fr not_active Expired - Fee Related
-
2002
- 2002-10-01 WO PCT/FR2002/003335 patent/WO2003029379A1/fr not_active Ceased
- 2002-10-01 AU AU2002350812A patent/AU2002350812B2/en not_active Ceased
- 2002-10-01 EP EP02785513A patent/EP1434829A1/fr not_active Withdrawn
- 2002-10-01 JP JP2003532606A patent/JP2005504164A/ja active Pending
-
2004
- 2004-04-02 US US10/815,914 patent/US20050059759A1/en not_active Abandoned
-
2008
- 2008-05-20 US US12/124,036 patent/US20080221247A1/en not_active Abandoned
Patent Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917607A (en) * | 1971-09-22 | 1975-11-04 | Shell Oil Co | Block copolymer adhesive compositions |
| US4394915A (en) * | 1982-04-12 | 1983-07-26 | Findley Adhesives Inc. | Hot melt adhesive compositions and bottle assemblies using said compositions |
| US5095059A (en) * | 1990-03-28 | 1992-03-10 | Mitsui Toatsu Chemicals, Inc. | Oiled-face adherable, hot-melt adhesive composition and a non-slip processing method of metal scaffolding board |
| US5266400A (en) * | 1990-04-20 | 1993-11-30 | Minnesota Mining And Manufacturing Company | Low voltage electron beam radiation cured elastomer-based pressure sensitive adhesive tape |
| US5120585A (en) * | 1990-10-12 | 1992-06-09 | Gelman Sciences Technology, Inc. | Package for preservative agent |
| US5120781A (en) * | 1991-05-07 | 1992-06-09 | Union Camp Corporation | Acid-modified polyhydric alcohol rosin ester tackifiers and hot melt adhesive compositions containing those tackifiers |
| US5496628A (en) * | 1992-11-25 | 1996-03-05 | Textiles Coated Incorporated | Single membrane insulation material |
| US5863977A (en) * | 1993-10-12 | 1999-01-26 | H. B. Fuller Licensing & Financing, Inc. | High molecular weight S-EB-S hot melt adhesive |
| US5910527A (en) * | 1994-04-28 | 1999-06-08 | Ato Findley, Inc. | Hot melt adhesive having a high acid number for disposable soft goods |
| US6582829B1 (en) * | 1996-03-14 | 2003-06-24 | H.B. Fuller Licensing & Financing Inc. | Hot melt adhesive composition comprising homogeneous ethylene interpolymer and block copolymer |
| US5939483A (en) * | 1996-07-12 | 1999-08-17 | H.B. Fuller Licensing & Financing, Inc. | Low application temperature hot melt with excellent heat and cold resistance |
| US6121354A (en) * | 1998-11-19 | 2000-09-19 | Bostik, Inc. | High performance single-component sealant |
| US6232391B1 (en) * | 1998-12-23 | 2001-05-15 | National Starch And Chemical Investment Holding Corporation | Multipurpose hot melt adhesive |
| US6926959B2 (en) * | 2000-01-31 | 2005-08-09 | H. B. Fuller Licensing & Financing, Inc. | Radiation curable adhesive compositions comprising block copolymers having vinyl functionalized polydiene blocks |
| US6291571B1 (en) * | 2000-03-21 | 2001-09-18 | Adco Products, Inc. | Lap edge roofing sealant |
| US6448303B1 (en) * | 2000-12-29 | 2002-09-10 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives for dermal application |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060229411A1 (en) * | 2005-04-06 | 2006-10-12 | Stephen Hatfield | Hot melt pressure sensitive adhesives based on blends of styrene/butadiene copolymers |
| WO2008028716A1 (fr) * | 2006-09-05 | 2008-03-13 | Henkel Ag & Co. Kgaa | Étiquettes redécollables |
| US9375895B2 (en) * | 2008-04-28 | 2016-06-28 | Sika Technology Ag | Hotmelt adhesives having an extended open time |
| US20110020634A1 (en) * | 2008-04-28 | 2011-01-27 | Sika Technology Ag | Hotmelt adhesives having an extended open time |
| US9695340B2 (en) | 2011-09-16 | 2017-07-04 | Henkel Ag & Co. Kgaa | Low temperature hot melt adhesive for high-speed coating and spiral coating |
| US20140199908A1 (en) * | 2011-09-16 | 2014-07-17 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
| US9816014B2 (en) | 2011-09-16 | 2017-11-14 | Henkel Ag & Co. Kgaa | Hot melt adhesive for disposable products |
| US9822283B2 (en) * | 2011-09-16 | 2017-11-21 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
| US10370567B2 (en) | 2011-09-16 | 2019-08-06 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
| US20140329074A1 (en) * | 2011-12-19 | 2014-11-06 | Sika Technology Ag | Reactive polyolefin hot-melt adhesive having low viscosity and use thereof for textile laminations |
| US9758704B2 (en) | 2012-08-28 | 2017-09-12 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
| CN115806789A (zh) * | 2022-09-26 | 2023-03-17 | 嘉好(太仓)新材料股份有限公司 | 一种用于口罩耳带粘接热熔胶及其制备方法 |
| DE102023126363A1 (de) | 2023-09-27 | 2025-03-27 | Tesa Se | Haftklebemasse und wiederablösbare Selbstklebeprodukte umfassend die Haftklebemasse |
| EP4621025A1 (fr) * | 2024-03-21 | 2025-09-24 | Colquimica-Indústria Nacional de Colas, S.A. | Adhésif thermofusible en granulés ou en perles pour coller les bouchons aux capsules et son procédé de fabrication |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005504164A (ja) | 2005-02-10 |
| WO2003029379A8 (fr) | 2004-04-22 |
| US20080221247A1 (en) | 2008-09-11 |
| WO2003029379A1 (fr) | 2003-04-10 |
| FR2830257B1 (fr) | 2006-12-01 |
| FR2830257A1 (fr) | 2003-04-04 |
| AU2002350812B2 (en) | 2007-11-15 |
| EP1434829A1 (fr) | 2004-07-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20080221247A1 (en) | Method of gluing hydrophobic and oleophobic substrates which are intended for packaging | |
| US9982171B2 (en) | Hot melt adhesive with functionalized metallocene catalyzed polyolefins | |
| AU757501B2 (en) | Hot melt adhesive composition comprising homogeneous ethylene interpolymer and block copolymer | |
| KR101507211B1 (ko) | 저온 적용 핫멜트 접착제 | |
| US20120165455A1 (en) | OBC Based Packaging Adhesive | |
| US10081212B2 (en) | Cohesively failing, non-staining hot melt adhesives | |
| US10227509B2 (en) | Hot melt adhesive composition for bookbinding | |
| CA2704960C (fr) | Composition d'adhesif thermofusible pour application a basse temperature et articles comprenant celle-ci | |
| EP3541887B1 (fr) | Composition adhésive thermofusible pour application à basse température et procédé comprenant une telle composition | |
| WO2015017704A1 (fr) | Composition adhésive thermofusible pour relier des paquets de récipients | |
| US20030091760A1 (en) | Adhesive for difficult to bond substrates | |
| JPH083526A (ja) | ホットメルト組成物 | |
| EP4332195B1 (fr) | Compositions adhésives thermofusibles à base de polypropylène | |
| US3661826A (en) | Wax compositions comprising petroleum waxes with certain hydrogenated two-block copolymers | |
| HK1150058B (en) | Low application temperature hot melt adhesive composition and articles including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: BOSTIK S.A., FRANCE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SAJOT, NICOLAS;POLLACCHI, BENOIT;SELLAK, SAIDA;REEL/FRAME:017212/0847;SIGNING DATES FROM 20051017 TO 20051109 |
|
| STCB | Information on status: application discontinuation |
Free format text: EXPRESSLY ABANDONED -- DURING EXAMINATION |